Phosphonium compounds



Patented July 18, 1944 assignments, to General Aniline & Film Corporation, New York, N. Y., a corporation of Dela-.-

ware

No Drawing. Application March 30, 1940, Serial No. 327,050. In Germany April 6, 1939 9 Claims. (Cl 260-389) This invention relates to a process for the manufacture of new quaternary phosphonium compounds of the following general formula The terms hydrocarbon radicals, aryl and phenyl radicals used in the specification and in the appended claims ar intended to cover the radicals as such as well as the radicals carrying substituents.

this way the halides of the phosphonium compounds are obtained. Other salts may be manufactured by the known methods, for instance, by doubledecomposition. Thus, for instance, in many case diflicultly soluble salts are formed by adding nitrates or thiocyanates to the aqueous solution of the halides. In many cases-the phosphonium compounds obtained may be substituted subsequently, for instance, by chloro atoms or by nitro groups.

The new phosphonium compounds represent colorless or weakly colored mostly well crystallizlng compounds whichmostly dissolve difficultly in cold water but'often show agood solubility in hot water. In organic solvents such as ether, acetic ester they are insoluble, easily soluble,

however, in alcohol. They display bactericidal Quaternary phosphonium compounds of the group consisting of.

hslogenC-B; and halogen-C-H Br RI wherein R4, Ra, Re and R1 stand for hydrocarbon radicals and Rrstands for an aryl radical'on a tertiary phosphine. In certain cases the manuobtained with the known phosphonium; compounds. 1 Thus, for instance, certain members of the new group of the phosphonium compounds show an increased fastness to washingor they.

surpass the known compounds as regards activity and protect not only against the attackof moths but also of other pests. for instance, anthrenus.

The following examples illustrate our invention without, however, restricting it thereto, the parts being by weight.

Example 1 parts of triphenylphosphine are heated in an autoclave with '70 parts ofphenyl-dimethyli'aoture may be performed by acting with halogenmethane derivatives upon tertiary phosphines 45 in which at least one radical is connected with the phosphorous. atom by a secondary ora tertiary carbon atom. The addition is effected suitably by heating if necessary in an acid medium, for instance, in the presence-of acetic acid. In

chloromethane for 12 hours to C. When cool the reaction mass is treated with water and Norit, filtered and the purified solution concen- ,trated in v'acuo;

Example 2 390 parts of 4-ch1orophenyl-phenyl chlorofiltered oil. On cooling the new phosphonium hol or mixtures and the fabrics are treated compound'crystailizes from the filtrate in white crystals.

' Example 3 Example 4 32 parts or phenyl-diethylphosphine are heated with the exclusion of air with 53 parts of triphenyl-chloromethane for 4 hours at 150 C.

' When cool the mass represents a brittle resin.

It is dissolved. in water, the solution separated from the residue and decolorized with Norit. The aqueous filtrate is evaporated to dryness in vacuo.-

Example 5 50 parts of triphenylphosphine-are heated in an autoclave with 30 parts of tertiary .butyl bromide for 8 hours at 145 C. The addition products separates in crystals.

'Ri-R-z stands for hydrocarbon radicals and Rsimpregnating the materials to be protected oc- For instance, the products are as water, alcotherecurs as usual. dissolved in suitable solvents such with at room or higher temperatures.

As further examples of the. new class of compounds may be mentioned the addition products of the following halogen-methane derivatives or triphenylphosphine:

3,4-dichlorophenylhenyl-chloromethane Di (4-ch1orophenyl) -chloromethane Phenyl-naphthy1-bromomethane 4-bromophenyl-phenylchloromethane i-chlorophenyl-diphenyl-chloromethane 4 -(N-methylbenzenesulfamido) -phenyl g phenylchloromethane 4' -(benzenesulfamido) phenyl phenyl chloromethane Tolyl-phenyl-chlorcmethane 2-chlorophenyl-phen lhloromethane 4-chlorophenyl-4-methoxyphenyl-chloromethane Z-chIorophenyI-di-(4-chlorophenyl) -chloromethane v 4-chlorophenyl-naphthyl-chloromethane Dimethyl-ethyl-bromomethane 4-nitrophenyl-di-phenyl-chloromethane 4-chlorophenyl-di-phenyl-chloromethane.

Example 6 100 kg. of woolen fabrics are treated in a dye bath 1:30 with (Ll-0.2% of the compounds obtainable according to Example 2 for half an hour at 60 C. Dyestuffs and dyeing agents may be added to the'bath. The fabrics, when dried, protected from the attack of moths.

We claim:

1. As new products the quaternary phosphonium compoundsoi the following general formula 13 B )acld radical wherein x stands for a radical selected from the group consisting of stands for an aryl radical. v

2. As new products the quaternary phosphm nium compounds of the following general formula halogen R X Br wherein x stands for a radical selected from the group consisting of /B| /R1 c-m and -c n Ri-R'r stand. for hydrocarbon radicals and Rs stands for an aryl radical.

3. As new products the quaternary phosphonium compounds of the following general formula V chlorine wherein x stands'for a radical selected from the group consisting of Ri-Rr stands for hydrocarbon radicals and Re stands foranarylradical. A

4. As new products the quaternary phosphonium compounds of the following general formula x chlorine R wherein x stands for a radical selected from'the group consisting of lti-Ra stand for aryl radicals. 5. As new products the quaternary phosphonium compounds of the following general formilk-Ra stand for an! ula wherein X stands for a radical selected from the group consisting of 6. As new products the quaternary phospho- 8. As a. new product the quaternary pholphonlum compounds of the following general tormnlum compound of the following formula,

ula

)ohlorine 5 B R f R1, m, m and 1% stand m phenirl radicals and As new met the em h 7 R1 stands for a. hydrocarbon radical. mum compoungof the 1011mm: ay: on)

'7. As a new product the quaternary phosphonlum compound of the following formula 1 

